Schooner Woodwind

2025 Sailing Season starts April 12th!

Father’s Day Brunch Sail

Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MD

Sail Dad away!  Guests can raise the sails, steer the boat, or just sit back and relax with a cold beverage. We sail past the Naval Academy and into the Chesapeake Bay. Fun for the whole family. Departing Annapolis Waterfront Hotel Dock at 11:00am and returning at 1:00pm. Maximum 30 guests on each sail. Includes ... Read more

$102.07

Tunes & Tales of the Golden Age of Annapolis (1765-1783)

Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MD

Tom plays 18th century fiddle tunes and shares social and political insights that made Annapolis the cultural center of the Chesapeake during the colonial era. History Monday Sunset Sails occur every Monday, May-September 21. Different topics and speakers vary throughout the season. Our bar includes a selection of Craft Beer, Wine & Bubbly available for ... Read more

Eastport and Its Importance to Maritime History

Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MD

Eastport, across the Spa Creek bridge, is a peninsula rich in maritime history. It's importance during wartime involved boat building for the US and its allies. Dating back to the Civil War, it maintained a hospital for soldiers with small pox. Originally, residents were immigrants, the working class, and farmers. The community today is better ... Read more

History of Shipping in the Chesapeake Bay

Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MD

Did you know that "ships" used to be about the size of the 70 foot Woodwind? Hard to imagine these days, join us as Mike Singer from the Baltimore and Chesapeake Bay Shipwatchers helps to weave a path from the small ships of yesteryear to the behemoths of today. History Monday Sunset Sails occur every ... Read more

Fireworks Cruise

Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MD

Join us for a festive cruise celebrating the 4th of July. We will depart from the Annapolis Waterfront Hotel dock at 6:30 pm for a sunset sail.  We will then anchor close to the fireworks barge for the 9:15 pm fireworks display and return to the dock after the show. Tickets include bottled water, soft ... Read more

$149.50

History of Watermen on the Chesapeake

Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MD

Annapolis is known as a seafood hub on the East Coast, famous for its crabs and oysters. But how many people truly know where their seafood comes from and how it is caught? For generations, Annapolis has been at the heart of the Chesapeake Bay’s seafood industry, sustained by the hardworking watermen who have navigated ... Read more

Event Series Birds of the Chesapeake Bay

Birds of the Chesapeake Bay

Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MD

Did you know that over 400 species of birds can be found throughout the Chesapeake Bay watershed? Join Jack Wildlife for a very special outing on the Chesapeake Bay in Annapolis to learn about the iconic bird species that call the Bay home, and many more fun facts and stories. You are all but guaranteed ... Read more

History of Shipping in the Chesapeake Bay

Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MD

Did you know that "ships" used to be about the size of the 70 foot Woodwind? Hard to imagine these days, join us as Mike Singer from the Baltimore and Chesapeake Bay Shipwatchers helps to weave a path from the small ships of yesteryear to the behemoths of today. History Monday Sunset Sails occur every ... Read more

Event Series Birds of the Chesapeake Bay

Birds of the Chesapeake Bay

Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MD

Did you know that over 400 species of birds can be found throughout the Chesapeake Bay watershed? Join Jack Wildlife for a very special outing on the Chesapeake Bay in Annapolis to learn about the iconic bird species that call the Bay home, and many more fun facts and stories. You are all but guaranteed ... Read more

Event Series Blackside of the Bay

Black-Side of the Bay

Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MD

Engaging conversation sharing the history of the Bay's ties to the slave trade with the knowledge and skills that elevated the region's standing as a global powerhouse in the maritime and seafood industries, "Experiencing Black-joy as an Act of Resistance during Jim Crow," and growth of the areas Black middle class . History Monday Sunset ... Read more

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